i know your problem is intermittent and as jim says, restarting eclipse helps when unplugging the usb and plugging it in again doesn't help. i did however find this extremely helpful detecting a new device: adb not finding my device / phone (macos x). give this a shot for your already discovered devices, to see if that helps.
sometimes adb fails to recognize devices properly. try "adb kill-server" and then "adb devices"
i had to download the android file transfer mac application, and then it worked fine. i also had to use the right usb cord -- some don't have a data channel.
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